Eleventh Time's a Charm
by Accidental-Ducky
Summary: During try number five, Coach had walked up to Derek and informed him that Stiles was like a son to him and that he had no problems beating the wolf right out of Derek with a lacrosse stick should Derek break Stiles' heart. The fact that Coach knew about the supernatural was more of a shock than the threat of bodily harm.


The first time Derek asked Stiles out, he thought it was some sort of joke and spent a good three minutes laughing until he registered the way Derek's eyebrows had dropped down and a creased had formed between them. He knew that position well, they were the Eyebrows of Disapproval, usually they followed some stunt or another that the werewolf didn't approve of (like that one time Stiles and Scott had dumped a bucket of pink glitter on his head).

Once he figured out that Derek was serious, Stiles straightened up and straight-up asked if Derek's coffee tasted suspicious because someone obviously must have drugged him at some point if he was actually considering Stiles for a date. When Derek stormed off, Stiles put it down to dosed coffee and carried on with his afternoon without thinking about it again.

The second time it happened was nearly a month later, Stiles lying in a hospital bed after being tossed through the air by a foul-tempered spirit that had most certainly not appreciated Stiles telling her that she was dead and should fuck right off back to the afterlife (heaven or hell, Stiles didn't give a shit as long as she stopped possessing random citizens and making them commit crimes around town).

Stiles had looked at Derek for a moment, as if couldn't quite understand what he'd just asked (and really, Derek thinks, even concussed, Stiles _has_ to know that a night at the diner equals date, right?) and then he turned to Scott and asked if he wanted to tag along. Derek cocked an eyebrow, Scott had the good sense to turn down the invitation, and Stiles told Derek to ask again when he wasn't seeing double.

Derek had hoped the old saying was true and that the third time really would be a charm when he asked Stiles out again. Unfortunately for him, it was the day he learned that Stiles had taught himself to sleep with his eyes open after Harris had slapped him upside the head one too many times.

Scott patted the older werewolf on the shoulder, offered up a bit of advice ("He's smart when it comes to figuring out lore and stuff, man, but he's completely oblivious when it comes to romantic attention"). Malia told him much the same thing when she passed by and apparently it took her climbing through his window and fucking him to really get the point across that she didn't want to be buddies.

Derek tried seven more times to ask Stiles out, and each of them ended worse than the last. During try number five, Coach had walked up to Derek and informed him that Stiles was like a son to him and that he had no problems beating the wolf right out of Derek with a lacrosse stick should Derek break Stiles' heart. The fact that Coach knew about the supernatural was more of a shock than the threat of bodily harm.

Finally, after an entire year of failed attempts, Derek just stopped asking. He decided to follow Malia's lead and use the most direct approach aside from emailing him Shakespeare's sonnets (he'd thought about it, but then Lydia told him he was an idiot).

After a particularly draining fight that ended with Derek being thrown out the library window (the school had a tip jar now that the pack would fill anytime they caused damage to the campus) and Stiles having to cut a wendigo's head off, the pair felt they were owed some hot chocolate and nearly collapsed in the booth once they finally made it to the diner.

Derek ordered for them, Stiles half-asleep and leaning heavily against Derek's side. He stayed pressed against Derek even when his hot chocolate was brought out, taking careful sips and trying not to burn his tongue too badly. Derek wasn't complaining, he liked the feel of the slighter man so close, the scent of fresh soap and exhaustion heavy in the air whenever Derek inhaled. There was something else there, the crisp scent of attraction that Derek has long associated with Stiles even when he'd threatened to rip his throat out with his teeth all those years ago.

The silence wasn't broken until the hot chocolate was gone and the staff were beginning to stack chairs, the manager sending them the stink eye until Derek gathered enough strength to stand. He grabs his wallet out of his pocket, counting out the needed amount and then adding an extra twenty as a tip since no one had complained about shutting down so late.

"How much is my part," Stiles asks. Derek has to fight against a smile at Stiles' clumsy attempt to dig his wallet out of the back pocket of his skinny jeans without standing up.

"My treat," Derek says easily, dropping the cash on the table.

"No, I can't let you do that. We'll split it and the tip." When he finally gets the wallet out, Derek snatches it right out of his hand and then slips it into the breast pocket of the plaid shirt Stiles had on. Derek could admit that he's grown fond of those shirts, though he drew the line at saying it out loud. "What the hell, man?"

"I was always told you don't split bills on the first date. See you later, Stiles."

And, as Stiles let out a strangled sound, Derek can't quite bite back a smug grin.


End file.
